My parents cat always came with us on family trips and we had TONS of them. And we always just left him unchaged and free to roam so he could walk to his litter box, use it, and then go sleep somewhere. But their were 4 people to watch him to make sure that he left my dad alone. With only me I am a little leary of leaving him uncaged because he might want to come cuddle or even worse go sleep by my legs. He might be just small enough or flexable enough to get under my leg and get something stuck under a pedal or to get stepped on when I am breaking or accelerating(more of the latter to be honest). I did try starting him in the cage and then letting him out once and he wouldn't even come out. So thats fine, he just flept in the cage with the door open and I liked that because then I could reach in and pet him every once in a while(I drive with one hand anyway). If he doesn't try being a lap cat or trying to sleep on the floor by my feet I might just put the litter box on the floor behind me and then let him roam. I have an suv so their is pleanty of room for him to explore things. Thats actually how I brought him home, lose in the car, but I held him the entire time. That was a fun 65 minute drive...not. I liked the bonding that happened but it was so hard to drive like that. I know I would have to cage him again at the boarder because I don't trust having the window open for that long with him out and running around. The last thing I need is for him to jump out the window at the checking station...that place is a zoo.
The last two trips he has stayed with my parents and has been absolutly fine while I was gone. And my parents love him to peices so they really don't mind watching him. Even my parents cat seems to like him...at least tollerate him. Tikki(my parents cat) is about 16 years old so he doesn't play that much any more and Tom doesn't stop playing so...their kind of polar opposites. But everyonce in a while Tikki will play with him and its so fun to watch. I just get a little nervice when Tikki decides to use tom as a chair and sit on him(tikki is pushing 20 pounds). So leaving him at my parents house isn't a problem its just Barb(my girlfriend) really wants to see him.
And no he has never been around me when I was doing anything like that with another person and he is VERY currious by nature so it will be interesting. Last time me and my girl were together we just stayed on top of all the blankets but I don't think thats going to be an option this time. Though Tom loves to attack things that are under the covers. Hopefully I can get a room with two beds that way me and Barb can have one bed and he can have the other with treats and toys on it. I think I might have to break my no treat rule so I can enjoy my time with my girlfriend. Being that I live about 700 miles from her we don't get that much time to be together so when I do see her things get pretty...involved